2,3-dimethoxy-N-(4-pyridinyl)benzamide | 667886-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-dimethoxy-N-(4-pyridinyl)benzamide
• 英文别名: 2,3-dimethoxy-N-pyridin-4-ylbenzamide
• CAS: 667886-02-4
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: MDMFDOVLGAFPGS-UHFFFAOYSA-N

物化性质

• 溶解度：
  >38.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-dimethoxy-N-(4-pyridinyl)benzamide 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,3-dihydroxy-N-pyridin-4-ylbenzamide
  参考文献：
  名称：

  Spectroscopic and Structural Investigations Reveal the Signaling Mechanism of a Luminescent Molybdate Sensor

  摘要：

  A heteroditopic ligand H-2-L consisting of a dihydroxybenzene (catechol)-unit linked via an amide bond to a pyridyl-unit and its methyl-protected precursor Me-2-L were synthesized, characterized, and their photophysical properties investigated. The three accessible protonation states of the ligand, H-3-L+, H-2-L, and H-L-, showed distinct H-1 NMR, absorption and emission spectroscopic characteristics that allow pH-sensing. The spectroscopic signatures obtained act as a guide to understand the signaling mechanism of the luminescent pH and molybdate sensor [Re-(bpy)(CO)(3)(H-2-L)](+). It was found that upon deprotonation of the 2-hydroxy group of H-2-L, a ligand-based absorption band emerges that overlaps with the Re(d pi)-> bpy metal-to-ligand charge transfer (MLCT) band of the sensor, reducing the quantum yield for emission on excitation in the 370 nm region. In addition, deprotonation of the catechol-unit leads to quenching of the emission from the Re(d pi)-> bpy (MLCT)-M-3 state, consistent with photoinduced electron transfer from the electron-rich, deprotonated catecholate to the Re-based luminophore. Finally, reaction of 2 equiv of [Re(bpy)(CO)(3)(H-2-L)](+) with molybdate was shown to give the zwitterionic Mo(VI) complex [MoO2{Re(CO)(3)-(bpy)(L)}(2)], as confirmed by electrospray ionization (ESI) mass spectrometry and X-ray crystallography. The crystal structure determination revealed that two fully deprotonated sensor molecules are bound via their oxygen-donors to a cis-dioxo-MoO2 center.

  DOI：

  10.1021/ic1019422
• 作为产物：
  描述：

  2,3-dimethoxy-N-(pyridin-4-yl)benzamide hydrobromide 在 四甲基氢氧化铵 作用下， 以 水 、 乙腈 为溶剂， 生成 2,3-dimethoxy-N-(4-pyridinyl)benzamide
  参考文献：
  名称：

  Spectroscopic and Structural Investigations Reveal the Signaling Mechanism of a Luminescent Molybdate Sensor

  摘要：

  A heteroditopic ligand H-2-L consisting of a dihydroxybenzene (catechol)-unit linked via an amide bond to a pyridyl-unit and its methyl-protected precursor Me-2-L were synthesized, characterized, and their photophysical properties investigated. The three accessible protonation states of the ligand, H-3-L+, H-2-L, and H-L-, showed distinct H-1 NMR, absorption and emission spectroscopic characteristics that allow pH-sensing. The spectroscopic signatures obtained act as a guide to understand the signaling mechanism of the luminescent pH and molybdate sensor [Re-(bpy)(CO)(3)(H-2-L)](+). It was found that upon deprotonation of the 2-hydroxy group of H-2-L, a ligand-based absorption band emerges that overlaps with the Re(d pi)-> bpy metal-to-ligand charge transfer (MLCT) band of the sensor, reducing the quantum yield for emission on excitation in the 370 nm region. In addition, deprotonation of the catechol-unit leads to quenching of the emission from the Re(d pi)-> bpy (MLCT)-M-3 state, consistent with photoinduced electron transfer from the electron-rich, deprotonated catecholate to the Re-based luminophore. Finally, reaction of 2 equiv of [Re(bpy)(CO)(3)(H-2-L)](+) with molybdate was shown to give the zwitterionic Mo(VI) complex [MoO2{Re(CO)(3)-(bpy)(L)}(2)], as confirmed by electrospray ionization (ESI) mass spectrometry and X-ray crystallography. The crystal structure determination revealed that two fully deprotonated sensor molecules are bound via their oxygen-donors to a cis-dioxo-MoO2 center.

  DOI：

  10.1021/ic1019422

文献信息

• Spectroscopic and Structural Investigations Reveal the Signaling Mechanism of a Luminescent Molybdate Sensor
  作者：Vincent A. Corden、Anne-K. Duhme-Klair、Sarah Hostachy、Robin N. Perutz、Nicole Reddig、Hans-Christian Becker、Leif Hammarström

  DOI：10.1021/ic1019422

  日期：2011.2.7

  A heteroditopic ligand H-2-L consisting of a dihydroxybenzene (catechol)-unit linked via an amide bond to a pyridyl-unit and its methyl-protected precursor Me-2-L were synthesized, characterized, and their photophysical properties investigated. The three accessible protonation states of the ligand, H-3-L+, H-2-L, and H-L-, showed distinct H-1 NMR, absorption and emission spectroscopic characteristics that allow pH-sensing. The spectroscopic signatures obtained act as a guide to understand the signaling mechanism of the luminescent pH and molybdate sensor [Re-(bpy)(CO)(3)(H-2-L)](+). It was found that upon deprotonation of the 2-hydroxy group of H-2-L, a ligand-based absorption band emerges that overlaps with the Re(d pi)-> bpy metal-to-ligand charge transfer (MLCT) band of the sensor, reducing the quantum yield for emission on excitation in the 370 nm region. In addition, deprotonation of the catechol-unit leads to quenching of the emission from the Re(d pi)-> bpy (MLCT)-M-3 state, consistent with photoinduced electron transfer from the electron-rich, deprotonated catecholate to the Re-based luminophore. Finally, reaction of 2 equiv of [Re(bpy)(CO)(3)(H-2-L)](+) with molybdate was shown to give the zwitterionic Mo(VI) complex [MoO2Re(CO)(3)-(bpy)(L)}(2)], as confirmed by electrospray ionization (ESI) mass spectrometry and X-ray crystallography. The crystal structure determination revealed that two fully deprotonated sensor molecules are bound via their oxygen-donors to a cis-dioxo-MoO2 center.